Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To 10 ml of carbon tetrachloride were added 2.72 g of 7-ACA, 4.3 g of a boron trifluoridediethylether complex, and 3.5 g of methanol. The mixture was heated at 60° C. for 35 min to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture was added 20 ml of cold water. Then, the mixture was adjusted to pH 7.5 with 28% aqueous ammonia at a temperature of 5° C. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings. The resulting mixture was applied to the same column as used in Example 2. The elution was conducted using water as an eluent. The resulting eluate was adjusted to pH 3.5 with 36% hydrochloric acid to hereby form a precipitate. The precipitate was collected by filtration, and washed with 5 ml of cold water and, then, with 5 ml of cold methanol to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.27 g. The yield of the desired product was as low as 11.1%.

Provenance & Evidence